EP0069696A3 - Derivatives of 9-fluoroprostaglandin, process for their preparation and their use as medicaments - Google Patents

Derivatives of 9-fluoroprostaglandin, process for their preparation and their use as medicaments Download PDF

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Publication number
EP0069696A3
EP0069696A3 EP82730087A EP82730087A EP0069696A3 EP 0069696 A3 EP0069696 A3 EP 0069696A3 EP 82730087 A EP82730087 A EP 82730087A EP 82730087 A EP82730087 A EP 82730087A EP 0069696 A3 EP0069696 A3 EP 0069696A3
Authority
EP
European Patent Office
Prior art keywords
alkyl
group
hydrogen
image
residue
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP82730087A
Other languages
German (de)
Other versions
EP0069696B1 (en
EP0069696A2 (en
Inventor
Werner Dr. Skuballa
Bernd Dr. Raduchel
Norbert Dr. Schwarz
Helmut Prof. Vorbruggen
Walter Dr. Elger
Olaf Dr. Loge
Michael-Harold Dr. Town
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Priority to AT82730087T priority Critical patent/ATE17475T1/en
Publication of EP0069696A2 publication Critical patent/EP0069696A2/en
Publication of EP0069696A3 publication Critical patent/EP0069696A3/en
Application granted granted Critical
Publication of EP0069696B1 publication Critical patent/EP0069696B1/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
    • C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Steroid Compounds (AREA)

Abstract

9-fluoroprostane derivatives of Formula I <IMAGE> (I) wherein R1 is CH2OH or <IMAGE> wherein R2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R1 is the residue <IMAGE> wherein R3 is an acid residue or R2 and A is -CH2-CH2- or cis-CH=CH-, B is -CH2-CH2-, trans-CH=CH- or -C 3BOND C, W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the alpha - or beta - position, D and E jointly are a direct bond or D is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, -C 3BOND C- or -CR6=CR7- wherein R6 and R7 differ from each other and each is hydrogen, chlorine, or alkyl, R4 is a free or functionally modified hydroxy group, and R5 is hydrogen, an optionally substituted aliphatic group, e.g., alkyl or halosubstituted alkyl, cycloalkyl, optionally substituted aryl or a heterocyclic group, and, when R2 is H, the physiologically compatible salts thereof with bases, have valuable pharmacological properties, e.g., as luteolytics or abortifacients.
EP82730087A 1981-07-03 1982-06-25 Derivatives of 9-fluoroprostaglandin, process for their preparation and their use as medicaments Expired EP0069696B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82730087T ATE17475T1 (en) 1981-07-03 1982-06-25 9-FLUOROPROSTAGLAND INDIVIDUALS, METHOD OF MANUFACTURE AND USE AS MEDICINAL PRODUCTS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3126924 1981-07-03
DE19813126924 DE3126924A1 (en) 1981-07-03 1981-07-03 9-FLUOR PROSTAGLAND DERIVATIVES, METHOD FOR THE PRODUCTION AND USE AS A MEDICINAL PRODUCT

Publications (3)

Publication Number Publication Date
EP0069696A2 EP0069696A2 (en) 1983-01-12
EP0069696A3 true EP0069696A3 (en) 1983-03-16
EP0069696B1 EP0069696B1 (en) 1986-01-15

Family

ID=6136403

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82730087A Expired EP0069696B1 (en) 1981-07-03 1982-06-25 Derivatives of 9-fluoroprostaglandin, process for their preparation and their use as medicaments

Country Status (14)

Country Link
US (2) US4454339A (en)
EP (1) EP0069696B1 (en)
JP (1) JPS588059A (en)
AT (1) ATE17475T1 (en)
AU (1) AU559449B2 (en)
CA (1) CA1218060A (en)
CS (1) CS236484B2 (en)
DE (2) DE3126924A1 (en)
DK (2) DK154073C (en)
ES (1) ES8304078A1 (en)
HU (1) HU190692B (en)
IE (1) IE53907B1 (en)
IL (1) IL66165A (en)
SU (1) SU1301308A3 (en)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822909A (en) * 1983-06-10 1989-04-18 Asashi Glass Company Ltd. 7-fluoroprostaglandins and process for their production
DE3325175A1 (en) * 1983-07-08 1985-01-17 Schering AG, 1000 Berlin und 4709 Bergkamen 11-HALOGEN PROSTANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
US4549980A (en) * 1983-10-11 1985-10-29 Mobay Chemical Corporation White modification of a bis-triazinyl amino stilbene optical brightener and a process for making the same
DE3347128A1 (en) * 1983-12-22 1985-07-11 Schering AG, 1000 Berlin und 4709 Bergkamen 9-HALOGEN- (DELTA) (ARROW HIGH) 2 (ARROW HIGH) -PROSTAGLAND IN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
DE3504044A1 (en) * 1985-02-04 1986-08-07 Schering AG, Berlin und Bergkamen, 1000 Berlin 9-HALOGEN PROSTAGLANDIN CLATHRATE AND THEIR USE AS A MEDICINAL PRODUCT
DE3510978A1 (en) * 1985-03-22 1986-09-25 Schering AG, Berlin und Bergkamen, 1000 Berlin NEW 9-HALOGEN PROSTAGLANDINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
DE3608088C2 (en) * 1986-03-07 1995-11-16 Schering Ag Pharmaceutical preparations containing cyclodextrin clathrates of carbacyclin derivatives
ES2054860T5 (en) * 1987-07-17 2003-11-01 Schering Ag DERIVATIVES OF 9-HALOGEN- (Z) -PROSTAGLANDINAS, PROCEDURE FOR ITS PREPARATION AND ITS USE AS MEDICATIONS.
US5891910A (en) * 1987-07-17 1999-04-06 Schering Aktiengesellschaft 9-halogen-(Z) prostaglandin derivatives, process for their production and their use as pharmaceutical agents
AU624078B2 (en) * 1987-07-17 1992-06-04 Schering Aktiengesellschaft Berlin Und Bergkamen 9-halogen-(z)-prostaglandin derivatives, process for manufacturing them, and their use as drugs
DE3831222A1 (en) * 1988-09-09 1990-03-22 Schering Ag 6-OXO-9-FLUOR-PROSTAGLANDIN DERIVATIVES PROCESS FOR THEIR PRODUCTION AND THEIR PHARMACEUTICAL USE
DE3923797A1 (en) * 1989-07-14 1991-01-24 Schering Ag 9-FLUOR-PROSTAGLANDIN DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR PHARMACEUTICAL USE
DE4024347A1 (en) * 1990-07-27 1992-01-30 Schering Ag CYCLOPENTANE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR PHARMACEUTICAL USE
US5385945A (en) * 1992-10-21 1995-01-31 Allergan, Inc. 7-(5-substituted cyclopentyl) and (5-substituted cyclopentenyl) heptyl alcohols, heptylamines and heptanoic acid amides, and method of lowering intraocular pressure in the eye of a mammal by administration of these novel compounds
US5721273A (en) 1993-12-15 1998-02-24 Alcon Laboratories, Inc. Use of certain 9-halo-13,14-dihydroprostaglandins to treat glaucoma and ocular hypertension
US5807892A (en) * 1994-09-30 1998-09-15 Alcon Laboratories, Inc. Use of certain prostaglandin analogues to treat glaucoma and ocular hypertension
WO1999002147A1 (en) 1997-07-09 1999-01-21 Androsolutions, Inc. Improved methods and compositions for treating male erectile dysfunction
US6103765A (en) 1997-07-09 2000-08-15 Androsolutions, Inc. Methods for treating male erectile dysfunction
US6593369B2 (en) 1997-10-20 2003-07-15 Vivus, Inc. Methods, compositions, and kits for enhancing female sexual desire and responsiveness
US5877216A (en) * 1997-10-28 1999-03-02 Vivus, Incorporated Treatment of female sexual dysfunction
WO1999021562A1 (en) 1997-10-28 1999-05-06 Asivi, Llc Treatment of female sexual dysfunction
US6235780B1 (en) 1998-07-21 2001-05-22 Ono Pharmaceutical Co., Ltd. ω-cycloalkyl-prostaglandin E1 derivatives
US20040266880A1 (en) * 2002-02-22 2004-12-30 Fumie Sato Antipruritics
US7737182B2 (en) * 2002-08-09 2010-06-15 Taisho Pharmaceutical Co., Ltd. Pharmaceuticals for xerosis
CN100408039C (en) * 2002-08-09 2008-08-06 大正制药株式会社 Antipruritic agent
AU2003301900A1 (en) * 2002-11-13 2004-06-03 Fumie Sato Antipruritic drug

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2628364A1 (en) * 1975-06-26 1977-01-13 Syntex Inc DL- AND 8R-9-FLUOROPROSTADIAL ACID DERIVATIVES AND PROCESS FOR THEIR PRODUCTION

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2950027A1 (en) * 1979-12-10 1981-06-11 Schering Ag Berlin Und Bergkamen, 1000 Berlin 9-CHLORINE PROSTAGLAND DERIVATIVES, METHOD FOR THE PRODUCTION AND USE AS A MEDICINAL PRODUCT

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2628364A1 (en) * 1975-06-26 1977-01-13 Syntex Inc DL- AND 8R-9-FLUOROPROSTADIAL ACID DERIVATIVES AND PROCESS FOR THEIR PRODUCTION

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMISTRY, BIOCHEMISTRY & PHARMACOLOGICAL ACTIVITY OF PROSTANOIDS, 1978, Seiten 39-60, Pergamon Press *
PROSTAGLANDINS, Band 16, Nr. 1, Juli 1978, Seiten 47-65 *

Also Published As

Publication number Publication date
DK294382A (en) 1983-01-04
JPH0443906B2 (en) 1992-07-20
US4454339A (en) 1984-06-12
AU8552882A (en) 1983-01-06
JPS588059A (en) 1983-01-18
ES513645A0 (en) 1983-03-16
DK123587A (en) 1987-03-10
CS236484B2 (en) 1985-05-15
CA1218060A (en) 1987-02-17
EP0069696B1 (en) 1986-01-15
DK154073B (en) 1988-10-10
ATE17475T1 (en) 1986-02-15
SU1301308A3 (en) 1987-03-30
IL66165A0 (en) 1982-09-30
EP0069696A2 (en) 1983-01-12
AU559449B2 (en) 1987-03-12
US4789685A (en) 1988-12-06
HU190692B (en) 1986-10-28
DE3126924A1 (en) 1983-01-20
DK123587D0 (en) 1987-03-10
ES8304078A1 (en) 1983-03-16
IE821611L (en) 1983-01-03
DK154073C (en) 1989-02-27
IE53907B1 (en) 1989-04-12
DE3268528D1 (en) 1986-02-27
IL66165A (en) 1986-01-31

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